Fungicidal substituted triazolylmethylcarbinols

Abstract

Fungicidal substituted triazolylmethylcarbinols of the formula ##STR1## in which n stands for the numbers 0 or 1, Ar stands for optionally substituted phenyl or for optionally substituted naphthyl, R 1 stands for hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkinyl, optionally substituted aralkyl, cycloalkyl or optionally substituted heteroarylalkyl, R 2 stands for alkyl, cycloalkyl, cycloalkylalkyl or alkenyl, R 3 stands for methyl and R 4 stands for methyl or R 3 and R 4 together stand for ethane-1,2-diyl, and addition products thereof with acids and metal salts. Intermediates of the formulas ##STR2## in which R 6 stands for alkyl having more than one carbon atom, cycloalkyl, cycloalkylalkyl or alkenyl, are also new.

What is claimed is: 
     
       1. A substituted triazolylmethylcarbinol of the formula ##STR1108## in which n stands for the numbers 0 or 1, Ar is phenyl which is optionally substituted by one or two identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 halogen atoms and straight-chain or branched halogenoalkoxy having 1 to 4 carbon atoms and 1 to 9 halogen atoms,   R 1  is hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms or is alkenyl having 2 to 4 carbon atoms,   R 2  is straight-chain or branched alkyl having 1 to 8 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or is straight-chain or branched alkenyl having 2 to 6 carbon atoms,   R 3  is methyl and   R 4  is methyl or   R 3  and R 4  together are ethane-1,2-diyl, or an addition product thereof with an acid or metal salt.     
     
     
       2. A compound or addition product thereof according to claim 1, in which R 1  is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl, pentyl or allyl, and   R 2  is straight-chain or branched alkyl having 1 to 6 carbon atoms, cyclopropyl or alkenyl having 2 to 4 carbon atoms.   
     
     
       3. A compound or addition product thereof according to claim 1, in which n is the number 0,   Ar is phenyl, phenyl which is substituted in the 4-position by fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy, or is phenyl which is substituted in the 2- or 3-position by a substituent selected from the group consisting of fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy and is optionally further substituted in the 4-position by fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy,   R 1  is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl, pentyl or allyl,   R 2  is alkyl having 1 to 6 carbon atoms or allyl,   R 3  is methyl and   R 4  is methyl.   
     
     
       4. A compound or addition product thereof according to claim 1 in which n is the number 1,   Ar is phenyl, phenyl which is substituted in the 4-position by fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy, or is phenyl which is substituted in the 2- or 3-position by a substituent selected from the group consisting of fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy and is optionally further substituted in the 4-position by fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy,   R 1  is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl, pentyl or allyl,   R 2  is alkyl having 1 to 6 carbon atoms, cyclopropyl or allyl,   R 3  is methyl and   R 4  is methyl.   
     
     
       5. A compound or addition product thereof according to claim 1, in which n is the number 0,   Ar is phenyl, phenyl which is substituted in the 4-position by fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy, or is phenyl which is substituted in the 2- or 3-position by a substituent selected from the group consisting of fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy and is optionally further substituted in the 4-position by fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy,   R 1  is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl, pentyl or allyl,   R 2  is alkyl having 1 to 6 carbon atoms, cyclopropyl or allyl and   R 3  and R 4  together are ethane-1,2-diyl.   
     
     
       6. A compound or addition product thereof according to claim 1, in which n is the number 1,   Ar is phenyl, phenyl which is optionally substituted in the 4-position by fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy, or is phenyl which is substituted in the 2- or 3-position by a substituent selected from the group consisting of fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy and is optionally further substituted in the 4-position by fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy,   R 1  is hydrogen, methyl, ethyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl, pentyl or allyl,   R 2  is alkyl having 1 to 6 carbon atoms, cyclopropyl or allyl and   R 3  and R 4  together are ethane-1,2-diyl.   
     
     
       7. A compound according to claim 1, wherein such compound is 6-(3,4-dichlorophenyl)-5,5-dimethyl-4-(1,2,4-triazol-1-yl-methyl)-1-hexen-4-ol of the formula ##STR1109## or an addition product thereof with an acid or metal salt. 
     
     
       8. A compound according to claim 1, wherein such compound is 1-(4-chlorophenyl)-2,2-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-heptan-3-ol of the formula ##STR1110## or an addition product thereof with an acid or metal salt. 
     
     
       9. A compound according to claim 1, wherein such compound is 6-(2,4-dichlorophenyl)-5,5-dimethyl-4-(1,2,4-triazol-1-yl-methyl)-1-hexen-4-ol of the formula ##STR1111## or an addition product thereof with an acid or metal salt. 
     
     
       10. A compound according to claim 1, wherein such compound is 1 (4-chlorophenyl)-2,2,4-trimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-ol of the formula ##STR1112## or an addition product thereof with an acid or metal salt. 
     
     
       11. A compound according to claim 1, wherein such compound is 1-(4-fluorophenyl)-2,2,4-trimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-ol of the formula ##STR1113## or an addition product thereof with an acid or metal salt. 
     
     
       12. A fungicidal composition comprising a fungicidally effective amount of a compound or addition product thereof according to claim 1 and an inert diluent. 
     
     
       13. A method of combating fungi which comprises applying to such fungi or to a fungus habitat a fungicidally effective amount of a compound or addition product thereof according to claim 2. 
     
     
       14. The method according to claim 13, wherein such compound is 6-(3,4-dichlorophenyl)-5,5-dimethyl-4-(1,2,4-triazol-1-yl-methyl)-1-hexen-4-ol,   1-(4-chlorophenyl)-2,2-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-heptan-3-ol,   6-(2,4-dichlorophenyl)-5,5-dimethyl-4-(1,2,4-triazol-1yl-methyl)-1-hexen-4-ol,   1-(4-chlorophenyl)-2,2,4-trimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-ol, or   1-(4-fluorophenyl)-2,2,4-trimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-ol, or an addition product thereof with an acid or metal salt.